by Lisa Hislop
This one is for the freelancers.
In my former life as a dating coach, if a client decided to end a relationship, I had them write a breakup letter detailing why they ended it and why they are better off on their own. The deal was, if they felt the impulse to reconcile, they had to read the letter first.

It occurred to me to write a similar letter when I hung my editor shingle, and it has helped me stay the course more than once. Allow me to explain.
Deciding to strike out on your own after years with the safety net of a paycheque is uncomfortably similar to leaving a long-term partner. When your life is busy, you’re feeling confident, and things are going well – it’s liberating. When they aren’t, it challenges everything you know about yourself.
More specifically, for the first several years on my own, I was learning how I edit at the same time as how I run a business. There were months when my marketing, networking, and editing abilities coalesced in a big payoff. Then, periods where the interminable scrimping and scraping caused me to doubt my knowledge base, my niche, and whether it was all worth it. At least once, I was working so hard that when a new client sent an inquiry, instead of relief, I felt resentment. Then, just like an ex promising they’ve changed, a comfy work-for-someone-else job came across my desk.
This is where the breakup letter comes in. To remind yourself that familiarity will always feel good while you’re on the brink, you’ll want to have a few important points sorted out ahead of time:
1. The voice of reason – three well-researched dates:
- a) The counter-rebound date marking the time you committed to spending on your own (in case going it alone is harder than expected).
- b) The time-until-profitable date you deemed feasible in your business plan (very practical).
- c) The make-or-break date specifying when money will start to run out (in case a consistent profit takes longer than expected).
2. The breakup story. Tell yourself why you left and the circumstances that would have to change for you to go back (no more breadcrumbs).
3. Be honest about the pitfalls. This is where you show yourself that you’ve thought through your fears about going solo and created contingency plans for if they come true.
4. Articulate your passion. List all the reasons why you love freelancing (editing, running a business, and the challenge of doing both at once).
5. Finally, make a list of supportive people to contact before you go back: a fellow freelancer, a business coach, and so forth.
If you’ve still got the entrepreneurial spark, the dates you’ve set will work like tinder. Seeing your own logical reasoning laid out on paper will reassure your mind so that creativity can flow, and you’ll be calling a friend for encouragement rather than to plan your escape. But if the work-for-someone-else job is the better move, the letter won’t stop you from taking a steady paycheque. It will simply help you stay objective about your dreams and your best interests if you do.
Lisa Hislop (she/her) is a professional editor specializing in short stories, collections, and anthologies. You can find her at www.theshortstoryeditor.com.
This article was copy edited by Vilma Indra Vitols, a freelance editor and opera singer based in Toronto.
